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Cheshire Vacation Packages

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Cheshire Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
Save 100% on your flight
Price was $829, price is now $492 per person
$492
per person
Jan 16 - Jan 19
found 15 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Book a stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chesterwood and Norman Rockwell Museum are located nearby.
Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $988, price is now $580 per person
$580
per person
Jan 16 - Jan 19
found 15 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Stay at this hotel in Great Barrington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount Ski Area are located nearby.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Save 100% on your flight
Price was $1,979, price is now $1,325 per person
$1,325
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
Book a stay at this luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Save 100% on your flight
Price was $815, price is now $556 per person
$556
per person
Jan 16 - Jan 19
found 15 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Book a stay at this spa hotel in Hudson. Enjoy free WiFi, a full-service spa, and a 24-hour front desk. Popular attractions Hudson Area Library and Stoddard Corner are located nearby.
Wilder House Berkshires

Wilder House Berkshires

2 out of 5
Save 100% on your flight
Price was $734, price is now $530 per person
$530
per person
Jan 16 - Jan 19
found 15 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Stay at this B&B in Sheffield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary are located nearby.
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $994, price is now $735 per person
$735
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions The Bookstore and Lenox Library are located nearby.
The White House Inn

The White House Inn

3.5 out of 5
Save 100% on your flight
Price was $989, price is now $732 per person
$732
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
Stay at this hotel in Wilmington. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions South Main Street and Pettee Memorial Library are located nearby.
The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Price was $926, price is now $708 per person
$708
per person
Dec 23 - Dec 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this business-friendly hotel in Schenectady. Enjoy free WiFi, free parking, and 5 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Rivers Casino & Resort and Scene One Movieland are located nearby.

Cheshire Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
Save 100% on your flight
Price was $829, price is now $492 per person
$492
per person
Jan 16 - Jan 19
found 15 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $988, price is now $580 per person
$580
per person
Jan 16 - Jan 19
found 15 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Save 100% on your flight
Price was $815, price is now $556 per person
$556
per person
Jan 16 - Jan 19
found 15 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Wilder House Berkshires

Wilder House Berkshires

2 out of 5
Save 100% on your flight
Price was $734, price is now $530 per person
$530
per person
Jan 16 - Jan 19
found 15 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)

Cheshire Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Stockade Historic District
Price was $926, price is now $708 per person
$708
per person
Dec 23 - Dec 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Save 100% on your flight
Price was $1,979, price is now $1,325 per person
$1,325
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
The White House Inn

The White House Inn

3.5 out of 5
Save 100% on your flight
Price was $989, price is now $732 per person
$732
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
South Shire

South Shire

4 out of 5
Save 100% on your flight
Price was $1,148, price is now $889 per person
$889
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

American Airlines
Wed, Jan 14 - Wed, Jan 28
CLT
Charlotte-Douglas Intl.
ALB
Albany Intl.
$179 Roundtrip, found 9 hours ago
$179
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Wed, Jan 14 from Charlotte-Douglas Intl. to Albany Intl., returning Wed, Jan 28, priced at $179 found 9 hours ago
Delta
Fri, Dec 12 - Mon, Jan 19
TPA
Tampa Intl.
ALB
Albany Intl.
$218 Roundtrip, found 5 days ago
$218
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Dec 12 from Tampa Intl. to Albany Intl., returning Mon, Jan 19, priced at $218 found 5 days ago
JetBlue Airways
Tue, Feb 3 - Mon, Feb 9
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$303 Roundtrip, found 11 hours ago
$303
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Tue, Feb 3 from Hartsfield-Jackson Atlanta Intl. to Albany Intl., returning Mon, Feb 9, priced at $303 found 11 hours ago
Delta
Thu, Dec 25 - Wed, Dec 31
SFO
San Francisco Intl.
ALB
Albany Intl.
$310 Roundtrip, found 4 days ago
$310
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Dec 25 from San Francisco Intl. to Albany Intl., returning Wed, Dec 31, priced at $310 found 4 days ago